Pyridine → 1-{[4-(3,3,3-Triphenylpropoxy)phenyl]methyl}pyridinium chloride

HRID 363706Notes

Reaction equation

HRID 363706 reaction equation
[C:1]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][Cl:16])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[Cl-:16].[C:1]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][N+:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 544382564-(3,3,3-Triphenylpropoxy)benzyl chloride

Product 1

HCID 675706061-{[4-(3,3,3-Triphenylpropoxy)phenyl]methyl}pyridinium chloride

Procedure

A solution of 4-(3,3,3-triphenylpropoxy)benzyl chloride, prepared in example 28, (210 mg, 0.51 mmol) in pyridine (1.0 mL) was refluxed for two minutes, and concentrated. The residue was recrystallized from acetonitrile-ethyl acetate and dried at 90° under high vacuum for 18 hours, providing the title compound as a monohydrate, a white powder, mp 155°-159° C. (212 mg, 86%). 1H NMR (CDCl3) δ 9.56 (d, J=7.5 Hz, 2H), 8.31 (t, J=7.5 Hz, 1H), 7.94 (t, J=7.5 Hz, 2H), 7.54 (d, J=8.6 Hz, 2H) 7.15-7.35 (m, 15H), 6.68 (d, J=8.6 Hz, 2H), 3.68 (t, J=7.7 Hz, 2H), 3.09 (t, J=7.7 Hz, 2H). Anal. calcd. for C33H30NO·Cl·H2O: C, 77.71; H, 6.32; N, 2.75; Cl, 6.95. Found: C, 77.47; H, 6.27; N, 2.63; Cl, 6.65.

Workup

  1. temperaturewas refluxed for two minutes
  2. concentrationconcentrated
  3. customThe residue was recrystallized from acetonitrile-ethyl acetate
  4. customdried at 90° under high vacuum for 18 hours

Sources & evidence

ORD record
ord-3001677308784aa8bb2273df9305a3f0
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

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